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    • 5 BR
    • 3 BA
    • 2 HF BA
    • Sleeps 9
    Estate #802737vb
    1
    Viewed 10 times in the last 48 hours
      Exceptional! 5.0/5
      (14 reviews)
      avg/night
      • 6 BR
      • 5 BA
      • Sleeps 20
      Estate #4258796
      14
      Viewed 174 times in the last 48 hours
        Exceptional! 5.0/5
        (17 reviews)
        avg/night
        • 6 BR
        • 4 BA
        • 1 HF BA
        • Sleeps 12
        Estate #629154vb
        17
        Viewed 9 times in the last 48 hours
          Wonderful! 4.9/5
          (15 reviews)
          avg/night
          • 6 BR
          • 6 BA
          • Sleeps 12
          Estate #568397vb
          15
          Viewed 29 times in the last 48 hours
            • 2 BR
            • 1 BA
            • Sleeps 6
            Estate #837730vb
            4
            Viewed 39 times in the last 48 hours
              Exceptional! 5.0/5
              (5 reviews)
              avg/night
              • 9 BR
              • 8 BA
              • Sleeps 16
              Estate #717669vb
              5
              Viewed 26 times in the last 48 hours
                Wonderful! 4.9/5
                (14 reviews)
                avg/night
                • 6 BR
                • 5 BA
                • Sleeps 10
                Estate #736279vb
                14
                Viewed 29 times in the last 48 hours
                  Exceptional! 5.0/5
                  (6 reviews)
                  avg/night
                  • 6 BR
                  • 5 BA
                  • 1 HF BA
                  • Sleeps 13
                  Estate #665300vb
                  6
                  Viewed 9 times in the last 48 hours
                    Wonderful! 4.8/5
                    (5 reviews)
                    avg/night
                    • 5 BR
                    • 4 BA
                    • 2 HF BA
                    • Sleeps 10
                    Estate #558988vb
                    5
                    Viewed 29 times in the last 48 hours
                      • 3 BR
                      • 5 BA
                      • Sleeps 10
                      Estate #830576vb
                      0
                        Excellent! 4.7/5
                        (23 reviews)
                        avg/night
                        • 3 BR
                        • 2 BA
                        • Sleeps 8
                        Estate #101832
                        23
                        Viewed 16 times in the last 48 hours
                          Wonderful! 4.8/5
                          (25 reviews)
                          avg/night
                          • 8 BR
                          • 5 BA
                          • Sleeps 16
                          Estate #387726
                          25
                          Viewed 89 times in the last 48 hours
                            avg/night
                            • 4 BR
                            • 4 BA
                            • Sleeps 10
                            Estate #721760vb
                            3
                            Viewed 30 times in the last 48 hours
                              avg/night
                              • 10 BR
                              • 9 BA
                              • 1 HF BA
                              • Sleeps 17
                              Estate #4174661
                              0
                              Viewed 21 times in the last 48 hours
                                • 5 BR
                                • 6 BA
                                • Sleeps 10
                                Estate #879089vb
                                0
                                Viewed 5 times in the last 48 hours
                                  • 5 BR
                                  • 5 BA
                                  • Sleeps 8
                                  Estate #850244vb
                                  0
                                    Exceptional! 5.0/5
                                    (11 reviews)
                                    avg/night
                                    • 6 BR
                                    • 5 BA
                                    • 1 HF BA
                                    • Sleeps 14
                                    Estate #661667vb
                                    11
                                    Viewed 33 times in the last 48 hours
                                      • 5 BR
                                      • 2 BA
                                      • Sleeps 10
                                      Estate #101843
                                      0
                                      Viewed 10 times in the last 48 hours
                                        Exceptional! 5.0/5
                                        (23 reviews)
                                        avg/night
                                        • 7 BR
                                        • 4 BA
                                        • 1 HF BA
                                        • Sleeps 16
                                        Estate #496513vb
                                        23
                                        Viewed 61 times in the last 48 hours
                                          avg/night
                                          • 8 BR
                                          • 4 BA
                                          • 2 HF BA
                                          • Sleeps 20
                                          Estate #836757vb
                                          2
                                          Viewed 68 times in the last 48 hours
                                            Exceptional! 5.0/5
                                            (8 reviews)
                                            avg/night
                                            • 7 BR
                                            • 7 BA
                                            • 1 HF BA
                                            • Sleeps 14
                                            Estate #174224
                                            8
                                            Viewed 16 times in the last 48 hours
                                              Exceptional! 5.0/5
                                              (8 reviews)
                                              avg/night
                                              • 7 BR
                                              • 9 BA
                                              • 1 HF BA
                                              • Sleeps 14
                                              Estate #100476vb
                                              8
                                              Viewed 10 times in the last 48 hours
                                                • 9 BR
                                                • 4 BA
                                                • 1 HF BA
                                                • Sleeps 16
                                                Estate #4215517
                                                0
                                                Viewed 5 times in the last 48 hours
                                                  • 8 BR
                                                  • 4 BA
                                                  • 1 HF BA
                                                  • Sleeps 18
                                                  Estate #296197
                                                  4
                                                    Wonderful! 4.8/5
                                                    (14 reviews)
                                                    View details for price
                                                    • 8 BR
                                                    • 4 BA
                                                    • 2 HF BA
                                                    • Sleeps 17
                                                    Estate #945611
                                                    14
                                                    Viewed 10 times in the last 48 hours
                                                      avg/night
                                                      • 7 BR
                                                      • 4 BA
                                                      • Sleeps 16
                                                      Estate #4199353
                                                      0
                                                      Viewed 27 times in the last 48 hours
                                                      • 1 - 26 of 26

                                                      Pittsfield: Vacation Rental Estates (26)

                                                       

                                                      Recent Pittsfield Reviews

                                                      Perfectly Fantastic Family Weekend

                                                      5 of 5
                                                      The Playhouse provides all that is necessary to have a fabulous time with family or a large group. I have looked for a place to hold our annual family Christmas gathering for quite some time and came across the listing for The Playhouse. Our annual holiday trip with our two grown children and their families to visit my husband's hometown and family in the Berkshires involved getting five hotel rooms and not enough room to enjoy everyone's company. The Playhouse fills this need in a wonderful way. The open areas are spacious and easily accommodated our large gathering on Saturday afternoon with brothers, sisters, nieces and nephews from 14 weeks to 70 years. On the main floor, the great room with it's open beams, beautiful lighting, wonderful views and great sound system was perfect setting for the adults at our gathering. Downstairs, the playroom area was great for the younger children to play ping pong and board games. Never once did we hear "I'm bored". The two kitchens are well equipped to handle cooking and serving food for our large group. The bedrooms are set up for convenience, comfort and a quiet retreat from activity. The mattresses and bedding are the best! Bathrooms plentiful and the heated floors much appreciated with 11 degree weather outside. The night we arrived we had eight inches of snow and the property manager Sean was there to dig us out first thing in the morning. He was informative upon our arrival and very responsive if we called him with a question. The property owner Daniel was also very accommodating and responsive. Much thought went into the planning and design of The Playhouse for beauty, comfort and function. Finally, my best recommendation is that we have already booked The Playhouse again for even longer stay next year.
                                                      • Submitted: Dec 21, 2016
                                                      • Stayed: Dec 2016

                                                      Serene and Beautiful Getaway in the Berkshires

                                                      5 of 5
                                                      My dearest friends and I wanted to get away from the world for a weekend, and Colesbrook Manor was just the place! As soon as we walked in the door we had a cozy feeling of being home. Andy has taken such great care in building a beautiful, warm, and peaceful oasis on this beautiful piece of property. We were truly delighted to sit by the fire, play music, and share a bottle of wine. We enjoyed exploring the trails and creek located right out the back door, as well as stargazing at night. The beds were cozy and the sauna was a treat, especially after taking a walk in the snow on Saturday. If you visit, check out the Dream Away Lodge (open seasonally from around April to Thanksgiving) for delicious food, a quirky atmosphere, and excellent music. However, we were happy that we bought groceries because we did not want to leave the house on Saturday. Andy, Thank you for being such an accommodating host and for building such a lovely home. We will be back!
                                                      • Submitted: Nov 29, 2016
                                                      • Stayed: Nov 2016

                                                      Beautiful house!

                                                      5 of 5
                                                      Laurie has done an amazing job with the house! We had a large group of family and everyone was comfortable. The barn has some great recreational activities which kept our group busy. The location is also very convenient being midway between the berkshires and the town of Hudson.
                                                      • Submitted: Nov 14, 2016
                                                      • Stayed: Nov 2016